A Perfect 4-Day Weekend in St. Barths

Fly in from Puerto Rico—Trade Winds Flight (short, 50 mins)

This is one of those journeys where getting there is already part of the experience. You’ll likely arrive in the late afternoon, enjoying one of the most scenic landings in the world. After checking into your hotel and settling into the island rhythm, make your way to L’Isola in Gustavia to kick off your St. Barths adventure.

Pro tip: Rent a car. Cars here are surprisingly inexpensive, and this island is best enjoyed when explored. No matter how fancy or sexy your hotel is, take the time to get out and experience both the vibrant life of Gustavia and the island’s more secluded beaches.

Dinner: L’Isola

Authentic Italian in the Caribbean, but incredibly refined. Don’t miss the gnocchi—they’re soft, delicate, and one of my must-haves every trip.

Morning: Hike to the natural pools

Start early before the sun gets too strong. The hike is moderate but rewarding—crystal-clear tide pools surrounded by dramatic rock formations. Bring water shoes!

Lunch & afternoon: Shell Beach

After the hike, head to Shellona on Shell Beach for a long Mediterranean-inspired lunch, Aperol spritz in hand. Stay for the breeze, the DJ, and the sun dipping behind the cliffs.

Dinner: La Petite Plage or Bagatelle

For Friday dinner, do the second sitting if you’re up for a party! Take your shoes off and feel the kinetic sand that won’t stick to your feet. Expect dancing on tables (don’t worry, they won’t fall), great music, and the perfect scene for groups and fun-seekers. An absolute must.

Morning: Zion Gym

After all that eating and drinking, I usually try to include a tropical workout to balance the indulgence. Zion is one of the best fitness spots on the island and worth checking out. It’s open-air, sandy-floor energy, great trainers, and overall vibe make it the perfect reset.

If gym is not an option, and you prefer some beach scouting, check out Seline Beach

Lunch: La Guérite

Start with the first seating for lunch here. The vibe is elevated yet relaxed, with great ambiance as the music picks up and the servers bring energy to match. After a few bites (and maybe a drink or two), head over to St-Jean Beach, one of the island’s most iconic beaches. Lounge, swim, and soak up the sun, or take a stroll toward Gyp-Sea or Nikki Beach for some people-watching.

Afternoon: Shopping in Gustavia

A fun fact that surprises most people I talk to: St. Barths is a luxury shopper’s paradise and a tax haven. From Louis Vuitton, Cartier, and Hermès to charming local boutiques, even window-shopping feels pretty glamorous. Better make sure you’ve saved a little extra. This is one island where retail therapy is part of the experience.

Evening: Drinks at Rémy Bar & dinner at Tamarin

• Pre-drinks: Rémy Bar at Eden Rock. This all-red, velvety, stylish bar makes you feel like you’re in a speakeasy right on the water. Treat yourself to a proper pre-dinner martini, or try their Negroni—also incredible.

• Dinner: Tamarin. A true island oasis. This is basically a lush tropical garden lit by lanterns, with winding pathways and a beautiful restaurant set right inside it. Romantic, stylish, unforgettable.

Mid-Day: Nikki Beach (second seating)

If you’re going to do Nikki Beach, do it on a Sunday and book well in advance. These types of reservations are where having a travel advisor (hi!) really helps.

Second seating is the way to go: more energy, more dancing, more Champagne showers. It’s the island’s weekly celebration of life.

No dinner reservation needed tonight.

I always say: after Nikki on a Sunday, you won’t want (or need) another reservation.

For a low-key end to the night, grab a to-go pizza from La Quintessence in Gustavia. It hits the spot, trust me. Or save this time for some in-room dining before calling it a night.

Before heading to the airport, enjoy a slow breakfast overlooking Gustavia at Carl Gustaf. Have your coffee overlooking the harbor in Gustavia. It’s the perfect, serene ending to a high-energy weekend.